10.1021/acs.jnatprod.8b01083.s001Corey
M. GriffithAbigail FeceuCynthia K. LariveDavid B. C. MartinSynthesis and Structure Reassignment of Malylglutamate,
a Recently Discovered Earthworm Metabolite2019American Chemical SocietysampleHMBCEarthworm Metabolite MalylglutamatediastereomerNMR spectra2019-02-08 20:19:22articlehttps://acs.figshare.com/articles/Synthesis_and_Structure_Reassignment_of_Malylglutamate_a_Recently_Discovered_Earthworm_Metabolite/7697942Malylglutamate, a newly identified
metabolite in earthworms, was
synthesized using a traditional peptide coupling approach for assembling
the amide from protected malate and glutamate precursors. The proposed
structure (<b>1</b>) and a diastereomer were synthesized, but
their NMR spectra did not match the natural sample. Further analysis
of the natural sample using HMBC spectroscopy suggested an alternative
attachment of the malyl moiety, and β-malylglutamate (<b>2</b>) diastereomers were synthesized, L,L-<b>2</b> and
D,D-<b>2</b>. NMR spectra were an excellent match with the natural
sample, and chiral-phase chromatography was employed to identify (−)-β-l-malyl-l-glutamate (<b>2</b>) as the isomer
native to <i>Eisenia fetida</i>.